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KlementineJBS / USYD_PhD_ELN

This repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's
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KBS37-1 - Synthesis of 2-acetyl-quinoline #118

Closed KlementineJBS closed 9 months ago

KlementineJBS commented 11 months ago

Link to HIRAC.

KBS37 - Synthesis of 2-acetylquinoline .docx

Reaction scheme

KBS37 - Synthesis of 2-acetyl-quinoline

Outcome

79.6 mg (0.465 mmol, 76%)

KlementineJBS commented 11 months ago

19/07/23

  1. Dissolved KBS35 (#113 ) (149 mg, 0.61 mmol) in dioxane (3 mL)
  2. Added aqueous HCl (1 M, 2.5 mL)
  3. Left stirring at 100 C from ~ 4 pm
KlementineJBS commented 11 months ago

TLC indicated completion at ~ 10 am.

Rotovapped dioxane off.

KlementineJBS commented 11 months ago
  1. Added some water (~ 10 mL) and extracted with ethyl acetate (3 x 10 mL)
  2. Washed with NaHCO3 (20 mL)
  3. Dried over mag sulphate and rotovapped down

Empty vial: 15.6699 Full vial: 15.7495 Mass: 79.6 mg (0.465 mmol, 76%)

KlementineJBS commented 11 months ago

H NMR

1H NMR (300 MHz, Chloroform-d) δ 8.21 (dd, J = 14.3, 8.5 Hz, 2H), 8.11 (d, J = 8.5 Hz, 1H), 7.85 (dd, J = 8.1, 1.5 Hz, 1H), 7.77 (ddd, J = 8.5, 6.9, 1.5 Hz, 1H), 7.63 (ddd, J = 8.1, 6.8, 1.2 Hz, 1H), 2.86 (s, 3H).

Doesn't appear to require columning, can be carried through to bromination step.

KBS37-1 cr_1.zip KBS37-1 cr.pdf